First time with sister's friend [mmf] | 2016

During my first year in college I had this friend called Dean. Dean was my first for many things. He was the first boy I kissed, he was the first blow job I gave, he was the first one to give me an orgasm. I'd go over to his place and we'd spend the afternoon naked in bed together and we would do everything except have intercourse.

I wanted my first time having sex to be special. I had already done everything else, I had even pierced my hymen. I had bought a vibrator and one night lying in my bed I'd inserted it fully and that's how I ended up popping my own cherry. I loved sex and even though I didn't love Dean I loved what we did together in bed. But I wanted to keep one last thing for a special night. I wanted to be sure I'd always remember the night it happened.

I lived in an apartment with my older sister. She was three years older than me and she would always hang out with these gorgeous guys. She would often bring her friends over on Friday nights and we would all hang out and play games and have fun.

One Friday night I had forgotten that her friends were coming over. I hadn’t seen Dean in a week and I was getting very horny so I had invited him over to spend the night. When he got to my place my sister’s friends were already there so we joined the party, thinking we would fool around later.

One of the people at the party was Omar. He was a new friend of my sister’s and it was the first time I ever saw him. He was in his mid-twenties, tall and muscular and he was very attractive. He had really dark skin and he shaved his head and he was so different from the guys my sister and I usually hung out with. I was immediately drawn to him and I spent most of the night close by his side to hear him talk. He was in law school and it was so cool to hear a guy who is that confident without coming off as an ass.

When people started a game of poker I pulled up a chair right next to him. I made sure to let him know I didn’t know how to play so he would feel like he had to help me out. Whenever he folded he’d look at my cards and make suggestions on how I should play my hand. I loved it because it gave me an excuse to touch him. If I lost I pretended to cry on his shoulder. If I won I’d squeeze his arm or his thigh or even, if I won really big, give him a peck on the cheek.

After an hour of play I had my hand always on Omar’s thigh. He liked that and he kept giving me this look and smiling at me. The way he looked at me was turning me on and my hand moved up until eventually it was touching his cock. Everyone was concentrating on the game so no one noticed but it was such a rush. Omar’s cock grew hard under my hand and I could tell he had a very big one! I was getting very horny stroking him under the table in front of everybody and I decided that tonight he would be my first, if he wanted to! The way he looked at me with my hand on his hard cock I had no doubt that he did.

I had butterflies in my stomach when the game ended and people started to leave. Eventually everybody was gone except my sister and her boyfriend, Omar, Dean and me. My sister said she was going to bed and told Omar that maybe he should leave but I said he could stay with me and Dean. She tried to insist but her boyfriend told her I was a big enough girl and she shouldn’t interfere. With me and Omar it was three against one so she gave up and she went to bed with her boyfriend while Omar, Dean and me stayed in the living room. Less than five minutes later we heard them having sex. The bed was creaking and my sister was moaning so I asked the two boys if they wanted to go to my bedroom since it’s on the other end of the apartment and that way we wouldn’t have to listen to them having sex.

I held both their hands and when we got to my bedroom Omar quickly shut the door. All three of us quickly realized that we all wanted sex. Omar put his hands on my hips and I backed my ass into him and felt his huge erection. Immediately his hands were on my hips and on my boobs.

I called Dean over to me and we started making out. My head was spinning as he put his hands on my cheeks and Omar reached inside my jeans to finger my pussy. I lifted my arms up and Dean took off my shirt while Omar pulled my pants down. They both squeezed themselves against me and their hands were all over my body as I kissed both of them.

They quickly took their clothes off and I got on my knees to suck them off. I’d sucked Dean off lots of times but Omar’s cock was much bigger and I gagged when I tried to take it to the back of my throat. I didn’t want him to know how inexperienced I was so I tried again and this time I managed to take it all in. I jerked him off with my hand while still sucking him and in no time he released his cum at the back of my throat.

My legs were wobbly went I got up. I handed Dean a pack of condoms and some lube and he lied down on the bed. I climbed on top of him and guided his cock inside my pussy. It was the first time I had a cock inside me and even though earlier I thought it would be Omar I still shivered in pleasure from Dean’s cock sliding in. I rode him hard and he grabbed my boobs and pinched my nipples while Omar grabbed my ass. With their hands all over me and Dean’s hard cock inside me I had my first orgasm in no time at all and I gasped as it washed over me.

I collapsed from exhaustion over Dean but he wasn’t finished so even though he was lying down with me on top of him he kept pounding into me. I relaxed and enjoyed the feel of his cock sliding in and out and soon I could feel a second orgasm start building up.

That’s when Omar reached for the bottle of lube and started spreading it all over my ass. He spread my cheeks and ran his lubed up finger over my asshole. I was on fire and I braced myself against Dean as Omar had me moaning when he pushed his finger in. I could feel Omar’s finger against Dean’s cock and it was so intense my moans got louder and louder.

I shivered when Omar pulled his finger out and placed the tip of his huge cock against my asshole. He was so lubed up it didn’t hurt but still I screamed in surprise when he pushed it in. The sensation of two cocks sliding in and out of me was almost too much to bear and I kept moaning and screaming while they fucked me.

I could feel Dean getting close and I knew my own orgasm was seconds away. It got unleashed when my bedroom door opened and I saw my sister’s boyfriend peek in on us. I screamed in ecstasy as he quickly apologized for disturbing us, saying that he’d knocked and I didn’t answer and my sister was worried about hearing me screaming that loudly. He was apologizing but he still stayed there long enough to watch me shake and writhe under the wave of my orgasm.

My pussy clenching around his cock also triggered Dean’s orgasm and I felt his hot cum shooting deep inside me. Omar pulled out as my sister’s boyfriend finally closed the door. He jerked himself as I lay on my back and released his second load over my tits and my lips. I licked Omar’s cum from my lips, tasting it fully for the first time.

After helping cleaning me up Omar grabbed his clothes and went to let my sister know I was okay before letting himself out. I put my head on Dean’s shoulders and in no time I was fast asleep.